Any user account that uses a roaming profile that upgrades the flash plugin for google chrome from 19.0.0.0.207 to 19.0.0.226 can no longer use the plugin properly.

Websites seem to think that flash is out of date, because you get an update message. When you disable the plugin altogether, you get the message to install flash.

Here is what you get when the plugin is disabled:

Then with the plugin v19.0.0.226 enabled you get this:

Then this:

When I roll back to 19.0.0.207 it is usable, however I do not want to use the version that is not secure. Affecting roughly 160 users on Virtual Machines. To clarify, I am able to use the plugin just fine on my VMs as long as the user profile is local, and not a roaming profile.

That's a good question for the Chrome forums, but the short answer is that Chrome has a couple update mechanism (full vs. component updater), and assets seem to show up in different places depending on the mechanism used.